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N-[(3S)-2-Oxotetrahydro-3-furanyl]undecanamide

Names

[ CAS No. ]:
216596-71-3

[ Name ]:
N-[(3S)-2-Oxotetrahydro-3-furanyl]undecanamide

[Synonym ]:
N-[(3S)-2-Oxotetrahydro-3-furanyl]undecanamide
Undecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-

Biological Activity

[Description]:

Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.

[Related Catalog]:

Research Areas >> Others

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
475.8±34.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H27NO3

[ Molecular Weight ]:
269.380

[ Flash Point ]:
241.5±25.7 °C

[ Exact Mass ]:
269.199097

[ PSA ]:
55.40000

[ LogP ]:
2.62

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.477


Related Compounds